


Halloween Adventure

by Wowfan5280



Category: Shall We Date?: Obey Me!
Genre: BDSM, Bondage, Casual Sex, Consensual Sex, Crossdressing, Double Penetration, Double Vaginal Penetration, F/M, Group Sex, Oral Sex, Rough Sex, Seduction, Time Travel, Vaginal Fingering, Vaginal Sex, blowjob
Language: English
Status: In-Progress
Published: 2020-02-19
Updated: 2020-02-19
Packaged: 2021-02-28 03:15:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,806
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22806949
Author URL: https://archiveofourown.org/users/Wowfan5280/pseuds/Wowfan5280
Summary: It is Halloween and the Demon Brothers along with Diavolo and Barbatos have a very exciting Halloween surprise for Sarah.
Relationships: Asmodeus (Shall We Date?: Obey Me!)/Original Female Character(s), Barbatos (Shall We Date?: Obey Me!)/Original Female Character(s), Beelzebub (Shall We Date?: Obey Me!)/Original Female Character(s), Belphegor (Shall We Date?: Obey Me!)/Original Female Character(s), Diavolo (Shall We Date?: Obey Me!)/Original Female Character(s), Leviathan (Shall We Date?: Obey Me!)/Original Female Character(s), Lucifer (Shall We Date?: Obey Me!)/Original Female Character(s), Mammon (Shall We Date?: Obey Me!)/Original Female Character(s), Satan (Shall We Date?: Obey Me!)/Original Female Character(s)
Comments: 3
Kudos: 28





	1. Halloween Adventure

**Author's Note:**

> Sarah is the name I used for my character in the game and it is my real name.  
> However, the character is named Sarah Ravencroft and her birthday is on Halloween.
> 
> Inspired by Race Through the Labyrinth by its_arch and Birthday Game by KieiJei.
> 
> Story is in first person perspective of my character.
> 
> Going to do different time eras for each brother as well as the last boss. Some of the characters the brothers are going to be playing as are fictional while others are non-fictional.
> 
> Enjoy!

It is Halloween and today is my birthday. I host a Halloween party every year except for this year due to the fact that I am currently in Devildom as an exchange student so I couldn’t host a party at my house.

 _I wonder where they are. I am sure they are around here somewhere_. I thought to myself as I entered the House of Lamentation by myself.

“Hello? Anyone here?” I called out. No response whatsoever. So I went looking in each and every room but no sign of the brothers anywhere. But then I remembered something that Diavolo told me. Diavolo had asked me about different human holidays several months ago and I also told him about my birthday and how I host different themes each year. I even told him about what themes I had been planning for the future.

“Well, we will make sure that you have a birthday that you will never forget.” Diavolo told me as I was about to leave for home.

Meanwhile, back in the present, I eventually made my way to my bedroom and noticed a present on my bed with a card.

**_**Happy Halloween and Happy Birthday Sarah! The others and I have a special Halloween Birthday Adventure for you. In this present is a special amulet. If you consent to what is about to go down as you like to say, then put the amulet on, grasp the crystal in your hand and say ‘I consent to what is about to transpire’. If you don’t, use the whistle to summon Barbatos and he will take you to the normal party. Hope you have fun in whichever option you choose. Sincerely Lucifer.** _ **

“So that’s where they are. I had a feeling something like this was up. Now this confirms it.” I said as I opened the package. There was a whistle, to summon Barbatos, and next to it was the amulet that Lucifer’s message mentioned.

“I am going to have fun. Fun with the brothers that is.” I said with a smile as I put the amulet on and grasped the crystal in my hand

“I consent to what is about to transpire.” I said out loud. Suddenly I was transported into a beautiful room with a bed, a shower, a large rectangular clock and a large mirror.

“Welcome Sarah,” said a voice behind me. I turned around and noticed Barbatos standing in front of me.

“Hi Barbatos! Did not expect to see you here.” I told him as he took several steps towards me.

“Well, it is part of the surprise after all. Anyways, I will now go over the rules with you. First, you cannot use your witchcraft powers unless it is an emergency. Second, you must complete the adventure within a week. Third, there will be a break in between the levels. These breaks do not apply to the time limit since time is frozen here. Lastly, enjoy yourself and have fun. Do you have any questions?” Barbatos explained as he took my hand and led me toward the mirror.

“No questions at all Barbatos.” I said as I looked at myself nervously in the mirror.

“Excellent. Now close your eyes and I will get your first costume ready.” He said. I closed my eyes and felt like I had my close magically change.

“You can now open your eyes.”said Barbatos as he stepped back from me. I opened my eyes and noticed I was in a neon pink, late Victorian era dress with a short skirt and a big bustle, a neon light blue late Victorian era corset, neon purple garter belt with same colored stockings, and a Victorian era choker.

“This is beautiful!” I exclaimed as I looked at myself in the mirror.

“You said these were your favorite colors and so it was arranged for all of your costumes to have these colors.” Barbatos explained.

“Awesome! Thank you so much.” I said.

“You’re welcome. Are you ready for your first adventure?” Barbatos asked. I nodded my head up and down to answer his question.

“Oh and before you go, I forgot to mention a few things. First there are seven levels, one for each brother, and also a boss level. Second, in order to get to the next level, you must reveal a magical item that looks like it does not belong. Third, in order to reveal the item, you must first defeat the bosses on each level. Lastly, in case of an emergency, use this whistle and it will bring you back here. Do I make myself clear?” Barbatos asked sternly as he handed me the whistle.

“Yes.” I responded, taking the whistle from him.

“Excellent. Off you go now.” He said with a smile. Suddenly, a Victorian style door magically appeared and Barbatos, being the very generous demon he is, opened the door for me and I went through the door and magically disappeared as the door closed.


	2. Jack the Ripper

**Summary for the Chapter:**

> First Level. Sadistically frightening Lucifer is the first as Jack the Ripper.

**Notes for the Chapter:**

> I actually have a fascination with Jack the Ripper. Not the murders themselves or his victims, but rather who he really was. The mystery surrounding his identity is fascinating to me.

I had gone through the door and felt like I was falling. When I landed, it was dark, cold and foggy. _G_ _uess I am not in Devildom anymore,_ I thought as I tried to see where I was. Despite of the fog, I noticed that I was in a city that looked like London, but I then noticed a sign that said White Chapel. My eyes grew big. This is where Jack the Ripper did a number of his killings. Truth be told, I was fascinated by Jack the Ripper not because of the murders, but because of the mystery surrounding his identity. No one knows who Jack the Ripper was and probably never will. In my personal opinion, Jack the Ripper was the most infamous serial killer of all time.

“Can’t believe it. I am in THE White Chapel. Can’t believe this is the place where Jack the Ripper started his killing spree.” I said excitedly as I started walking down the street all the while trying to find the item that will take me to the next level. As I was walking, a policeman was walking in the opposite direction.

"Hey miss! It is a bad idea to be out here at night. Don't you know about Jack the Ripper?" a policeman asked me as we passed each other on the street.

"I do know about him but I am not afraid. I can handle myself." I said in my best British accent as I turned to face him.

"Alright then. Be careful and keep your guard up." He responded as he started to walk away, continuing his beat.

 _That was close,_ I thought as I continued on my way. Suddenly I heard a whistle coming from a distance. So I started heading in the direction of which the whistle came from.

“We have another one!” I heard a man shout. So I ran toward that direction and saw a bunch of police men surrounding a crime scene.

"Who is it this time?" One of the police man asked.

"Its Annie Chapman this time." Another officer replied. They continued talking as I slowly walked away. I was able to get away from the crime scene without being noticed. I kept walking the streets until night time. 

Men tried to have me have sex with them during my walk, but I refused and told them that I was looking for a certain friend of mine who is also a client of mine. They all backed off when I told them that. At night time, things were quiet and really hard to see except for the street lamps that lit up the street.

"Its night time and still don't know where my birthday/Halloween surprise is." I muttered to myself. Suddenly, I felt a cold breeze on my arm and on my neck.

"Aren't you supposed to be in bed?" A sinister voice that had a very strong British accent that sounded like it came from behind me asked.

"I am having trouble sleeping." I replied as I started to walk away. However, the sinister presence followed me. 

_Gotta find a way to lose him,_ I thought. So I ran in all different directions in order to lose him. However, he kept following me that is until I ducked into an alleyway that was pitch black. Although I could see him, he couldn't see me. As soon as he passed me, I quietly peeked around the corner to see if he was gone.

"Good. He's gone." I whispered as I started running in the opposite direction. Little did I know that he would find me eventually. So I kept on running until I was out of breath. I walked the rest of the way down the street. 

"I know you're somewhere bitch! You can't hide from Jack the Ripper!" I heard him say as I turned a corner. I decided to run when I heard his voice. I kept running every which way going in a zig-zag motion.

"Come out, come out wherever you are." He taunted as I kept running away from him. I had to take a break from running since I was out of breath.

"Gotcha!" He said as he grabbed my arm.

"Let me go!" I shouted quietly. I did what I had to and kicked him in the groin. He bent over and I was able to get out of his grasp and I ran. That was the first time I saw him up close in person and I felt that there was something familiar about him. I had kept running until I tripped up on a loose cobblestone that was on the cobblestone road.

 _Dang it. I had to trip up and hurt my ankle_ _now_ _,_ I thought angrily to myself.

"Gotcha this time bitch." The sinister figure said as he somehow knocked me unconscious. He then picked me up and carried me to who knows where. As soon as I woke up, I noticed that I was blindfolded and could feel my wrists bound and could still feel the pain in my ankle that I injured while running from the creep who was chasing me.

"Where am I?" I asked.

"Well, look who has finally woken up. You,my dear, are in my secret chamber." The sinister voice explained as I could hear him approach me. As soon as he approached me, he lifted my chin up to probably look at his face, even though I had a blindfold on.

"Who are you?" I asked.

"I will give you a hint. Annie Chapman was my third." He replied.

"Jack the Ripper. But what do you want with me?" I asked.

"Your soul as well as to make you another one of my victims. It would be an extreme pleasure to kill a witch.” He replied as he got out his knife.

"I am more powerful than you Jack!" I shouted as I tried to use my magic. " What the!?" I exclaimed.

"I used the anti magic binding spell on you when I knocked you out. So now my dear, I will show you just how dangerous I can be.” He said as he pulled my chin up toward his face. He proceeded to kiss me deeply while his hands explored my body. I held still while he felt my body up. Jack kissed my neck and licked it as well. He moved down to my chest area and massaged my breasts with his hands. His hands felt smooth against my dry skin. He licked my left nipple while he pinched the right nipple with his right hand all the while his left hand rubbed against my clit. He then licked my right nipple as he pinched my left nipple with his left hand while his right hand rubbed my clit. Once he was done with my breasts and nipples, he then moved down to my clit. He lifted my legs so he could kiss and lick my clit.

”Fuck! Fuck me Jack!” I shouted as Jack rubbed and kissed my clit.

”Not yet my pretty.” He said in a sinister tone as he resumed to rub and kiss my clit. He inserted his fingers into my entrance and started to thrust in and out.

"P...Please I need you in me!" I screamed in ecstasy. 

"You're impatient aren't you? You will get what you want in due time." He said as he continued thrusting his fingers into me. Jack pulled out his fingers and put my legs down. Just when I thought I was going to have a break, he pulled my head up and put his cock right in front of my mouth.

"You need to be a good girl and lick. Otherwise, I will kill you." He said. Scared for my life, I started to lick the tip of his cock and the pre-cum that was coming from it. My tongue swirled around the tip like it was a lollipop.

"Good girl." He said with a smirk on his face. He then proceeded to open my mouth and inserted his cock.

”Suck.” He demanded. I did what I told and sucked on his cock as he was pushing my head back and forth. I was afraid of throwing up on him since my gag reflexes are extremely sensitive. However, I did not and continued to suck his dick until he removed it from my mouth.

“I...I need you! Inside me! Please!” I cried out in frustration.

”Since you’ve been a very good girl, I will give you what you want.” He responded in a sexual manner. He picked up my legs and had me wrap them around him, which I did. He proceeded to line the tip of his cock up with my entrance. Soon he started thrusting slowly but eventually sped up the pace.

”I...I’m about to cum!” I screamed.

”Good because I’m about to cum as well!” He said as he kept his thrusting. Eventually, I could feel his cum inside of me getting filled up all the way. We both had reached climaxed before becoming exhausted. Jack put my legs down and then fell to the floor himself.

"You are now free since you have pleasured me in a way that none of my victims ever did." He said as he got up and untied the bindings on my wrists.

"Why is that?" I asked as I massaged my wrists after that adventure.

"You have are unique in a way that they were not." He responded panting heavily.

:"I want to know your true identity." I told him as my panting nearly subsided.

"You already know me." Jack replied as he started to get up.

"May I see who you are?" I asked. 

"Yes of course." Jack replied as he started taking off my blindfold. As soon as he took it off, I looked up and saw that Jack the Ripper was actually Lucifer.

"Lucifer? Really?" I asked in surprise. He nodded with a friendly smile on his face and his eyes closed.

"Yes it is me. Did you like the surprise?" Lucifer asked in his normal voice.

"Yes I did my love." I responded as he came closer to me. He then helped me up and got me cleaned up the best he could. We took a short nap after all that.

"Do you know where the magical item is so I can unlock the next level?" I asked as I was getting up from the mini nap. He turned around behind him and gave me what looked like a money bag. After seeing the money bag, I guessed that Mammon was next. So I gave Lucifer one final kiss before taking the money bag and disappeared.

I ended up back at the room where I got ready and I looked at the clock and it said 5 hours spent. I sighed in relief since I only had a week to complete this adventure. 

"Did you have fun?" Barbatos asked as he approached me. I nodded yes since I was too tired to respond. " Well you might as well get cleaned up and get something to eat and rest up. Don't worry about the time since this room is frozen in time." He then waked away so I could have some privacy. I got cleaned up and had something to eat. Barbatos entered the room and asked me if I was ready for the next adventure.

"I am ready." I replied. Soon I was magically dressed as a 1920's flapper. The dress was neon purple and had tassles, the garter belt and stockings were neon blue and the shoes and the headband with the feathers were neon pink. Soon I was ready to go and Barbatos opened another door and I stepped inside and magically disappeared as the door closed, just like before.


End file.
